Very interesting thread indeed, as it is a recurrent matter in various discussions here. I love that it hasn't become a pissing contest yet. Let's keep it this way
So let's go with the cities I've visited / There is a gap in the Prairies obviously, as I alway flew over them... Project for the future I guess!
From East to West / WARNING : subjective material below. Thin-skinned people : back off please
St. John's | Attractive, colourful, vivante, kind of folkloric, best pub scene, mysterious, makes me want to wander and discover more of it (by foot mostly)... It's kind of a nest of life amongst surreal, magnificient yet harsh landscape (I've seen icebergs - quite a surprise for a Montérégien such as myself).
Halifax | Feels international, important harbour ambiance (caractère portuaire très prononcé, qui m'a rappelé certains secteurs de Boston et Portland), sea smell and seagulls, surprisingly small as it feels way bigger than it actually is... Halifax has this capital city vibe; rich, cultural, old and new... My very first impression from the citadel was that it felt a bit scandinavian (it didn't last long and was mostly due to the architecture of St. Paul's steeple).
Moncton | Felt small, new and quite horizontal... More like a town than a city. However, despite its so-so character (my sole opinion here), we manage to feel that the ocean isn't that far away; maybe it's the smell, maybe it's the apparent joy that I felt from Monctoners. Loved the light and the strands.
Saguenay | Surprisingly alive and impressively urban for its location. The warmth of the population contrasted with the fjord and the landscapes.
Québec | The closest to Europe I've ever felt in North America. The inner neighbourhoods are human-scaled and very intimate. A mix between tradition and innovation. Foody, quite trendy, cultural and a bit snobbish. It has this big city feel and bones (for North America) that are reversely considered to the ambiance of a big provincial town by Europeans. It simply is an amazing place (despite the galloping sprawl).
Sherbrooke | Exhausting, hilly, surprisingly small and sprawly. Students everywhere - party vibe downtown.
Trois-Rivières | A rough diamond. Torn up between its industrial past and its cultural renewal. I got a proletary vibe that Sherbrooke, for example, doesn't seem to have, at least downtown.
Montréal | I actually am biased on this one, as I've lived there for 10 years. However as a néo-montréalais, I've alway found that city extraordinary, dense but very liveable, walkable, sunny, tense especially around the east/west divide, intercultural, worldly and classy. You feel the history and the former importance and past glory. One thing which struck me above all else is how Montreal is in fact a collection of villages -each with its very own vibrant heart and monumental church- that grew into each other.
Ottawa | Very walkable and friendly, even when you speak French
, cultural but too tidy and organized. As a francophone I was quite shocked that the parliement was turning its back to French Canada when I first visited.
Gatineau | Felt like a former gem that was destroyed - post-war feel especially on Hull island. I felt bad.
Kingston | A kind of epitome of the canadian town. Downtown and the old neighbourhoods are amazing, and you get this impression of importance.
Oshawa | Endless sprawl and jammed highways. Sea of beige cladding. Didn't make a strong impression to me. Maybe it's liveable, but I wouldn't bother to try to know...
Toronto | Eclectic, young, vibrant, windy, cosmopolitan, hard-trying, segregated and ambitious metropolis where everything seems possible (but I was surprised to be able to find myself surrounded by sfhs quickly outside the core). Le contraire de Montréal : feels like a provincial town that quickly grew into an alpha city and tries hard to adapt itself to its newfound glory.
Hamilton | The best testimonial to the canadian industrial history with everything that comes with it (architecture, history, urban forms and scales), unfortunately badly treated. Edgy city on the path to renewal.
St. Catharines | -_-
Calgary | Ambitious and VERY proud of itself. A nice balance between nature and urbanity. It also felt american to me (Single-family housing neighbourhoods where the garage seems to be bigger than the actual house, car and power center culture, etc.) Distant people (for example that don't kiss on the cheeks or really hug when they first meet... ça me rend mal à l'aise lorsque vient le temps d'interagir).
Vancouver | Felt foreign to me (for example, Calgary didn't) for whatever reason. A kind of San Francisco of the north especially because of the geography and the natural light. Soft, apparently liveable, artsy, laid-back and sporty...
Victoria | Charming, classy, confortable, well-scaled and very friendly city that I don't want to leave everytime I go.